Carbene and photocatalyst-catalyzed 3-acylation of indoles for facile access to indole-3-yl aryl ketones

• Published in: Chemical communications (Cambridge, England) England), 2024-10, Vol.6 (79), p.1188-1191
• Main Authors: Tu, Ting, Nie, GuiHua, Zhang, Tinglei, Hu, ChunMei, Ren, Shi-Chao, Xia, Huimin, Chi, Yonggui Robin
• Format: Article
• Language: English
• Subjects: Acylation; Aromatic compounds; Carbenes; Chemical synthesis; Cross coupling; Functional groups; Indoles; Ketones; Photocatalysts; Reductases; Substrate inhibition
• ISSN: 1359-7345; 1364-548X; 1364-548X
• DOI: 10.1039/d4cc03257h

3-Acyl indoles play important roles in both organic synthesis and diverse types of functional molecules. Herein, a facile nitrogen heterocyclic carbene (NHC) and photocatalyst cooperatively-catalyzed 3-acylation of indoles was disclosed. The reaction proceeded via radical cross-coupling of indole-based aryl radical cations with NHC-bound ketyl radical species, which are less explored in radical NHC catalysis. The reaction exhibits mild reaction conditions, broad substrate scope, and good functional group tolerance. Mechanistic studies support our proposed reaction pathway. The synthesis of structurally diverse analogs of an aldose reductase inhibitor and antibacterial activity investigation further demonstrated the utility of the current acylation reaction. A carbene and photocatalyst-catalyzed 3-acylation of indoles was disclosed, providing access to indole-3-yl aryl ketones, which play important roles in both organic synthesis and diverse types of functional molecules.